3. Leak (or reiterate) that he would sit out games
If Damian Lillard wanted to take applying pressure a step further, he and his camp could reiterate or leak through the media that he would sit out games if his trade request or demand wasn’t met by the Portland Trail Blazers. There have been subtle hints of what Lillard may or may not do in the event that he isn’t traded, but there hasn’t been a clear indication either way. Ultimately, the belief is, based on his character as a professional, that Lillard would not sit out games.
And that may be something the Blazers are betting on. Portland could be buying time to possibly get Lillard to either move off his trade request or be willing to play with the Blazers until his request is made. Deep down, with everything that has been reported, it would not be surprising if that was an ideal outcome for the Blazers at the moment.
If Lillard were to say (through a reporter) that he is willing to sit out games, that perhaps changes the entire complexity of this situation. I’m not saying it would force the Blazers to succumb to his every demand, but it would certainly force their hand a bit with training camp inching closer and closer.